Okay, I've talked to some of the experts here at this forum - so here's my suggestion to fix your iPad syncing problems.
To verify, this is the message you get from iTunes: "Itunes cannot read the contents of the iPad. Go to the summary tab in iPad preferences and click restore to restore this iPad to factory settings." Correct?
If this is what the message says, it appears your iTunes sync with your iPad has somehow gotten corrupted. So, you'll need to remove some files so that iTunes can rebuild the sync files. Here's how:
1. Using iFile, or OpenSSH and an SCP program such as WinSCP, navigate to this address on your iPad:
/var/mobile/Media/iTunes_Control/iTunes
1.1. Within this folder, there is a file titled iTunesCDB. Make a copy of this file for backup (just in case this method doesn't work - always make backups!). Then, delete this file.
1.2. By deleting this database file, all your music and video files on the iPad are now orphaned. Meaning, your files are still on your iPad, occupying space, but iTunes doesn't know what they are now. So, now you've got to remove all your music and video files from the iPad.
2. Go back one level in iFile (or the WinSCP program) to this address:
/var/mobile/Media/iTunes_Control
2.1. Select the folder Music and then delete all the folders within this folder (leave the Music folder there; just empty it)
3. Now, you should be able to sync to iTunes.
You will have to select/re-sync all your music and videos (if any) back to the iPad from iTunes. Depending on the size of your collection, this may take some time. Just give it that time - don't attempt to disconnect the iPad until the sync is done (some of my research states this may be one of the reasons the sync gets corrupted).
I hope this helps. Honestly, I hope it works! It's the only way I know of to fix your iTunes sync problem - but there is no way for me to test this for you. Good luck and let me know how it works.
Marilyn